


That Damn Dress

by Useless_Fanfictions



Category: Supernatural
Genre: Blow Jobs, Brother/Brother, Cock Slut, Crossdressing, Crossdressing Kink, Crossdressing Sam Winchester, Dress, Emotional Hurt/Comfort, First Time Blow Jobs, Hiding, Hiding Secrets from parents, Incest, Kissing, M/M, Making Out, Pre-Series Dean Winchester, Pre-Series Sam Winchester, Prompt Fic, Prompt Fill, Queer Sam Winchester, Rough Oral Sex, Rough Sex, Sam Winchester Needs a Hug, Sam Winchester has a Sexuality Crisis, Sam Winchester in a dress, Sam steals women's products, Secrets, Thief Sam Winchester, Underage - Freeform, Underage Kissing, Underage Sex, mastubation, minor identity crisis, prompt, slut kink
Language: English
Status: Completed
Published: 2019-07-24
Updated: 2019-07-24
Packaged: 2020-07-18 00:14:07
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 18,204
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19965550
Author URL: https://archiveofourown.org/users/Useless_Fanfictions/pseuds/Useless_Fanfictions
Summary: Anonymous prompt:Can I get some teen sam figuring out what it’s like to crossdress?? Plz have some wincest as well but its okay if there is none. Maybe John catches him maybe he doesn’t. can Sam pretty please have a slut kink too? I like happy endings.Or,The one where Sam just wants to be himself and love his brother.





	That Damn Dress

**Author's Note:**

> Hello everyone! 
> 
> Let's just chat for a second before everyone starts in with the judgment here. And yes, I have to word it like that because I have gotten a lot of crap for this fic and it's ridiculous. 
> 
> I am aware that this is incest and incest is generally frowned upon. I understand completely. Except, these are fictional characters. This whole fic is nothing but fiction and none of it is real. These characters are open for any type of interpretation. For me, I prefer to write Destiel or Sabriel, but I will write the occasional Wincest and be proud of it because this is my writing. If you are not proud of your writing, then you shouldn't be a writer.
> 
> Now, that being said. This is a prompt that I got a while ago, and I mean a _while_ ago, back when I first started writing Supernatural fanfictions on Wattpad when I was almost fifteen. So years ago. I picked up this prompt and wrote it then and it was absolute shit. As someone who has/will also be improving her writing, I can say that the original version of this was terrible. 
> 
> I found this saved on my google account and I cringed the entire time reading. So I searched a while for the original prompt and found it and definitely had to re-write it. Now, I am proud of this. Let me know what you guys think!
> 
> Back then, when I had a lot of my real-life friends on my Wattpad, I got a lot of crap for it being incest. And me being my awkward, young-teenage self, I couldn't properly articulate how I don't actually believe incest is a good thing and how these were just fictional characters. So I took it down and couldn't stand to look at it for a while. But now I don't care, and to all those people who want to judge (irl or internet people) fuck off, I'll write what I want to.
> 
> ~~~
> 
> To the person who left the prompt (you know who you are), you have waited a long time for me to properly fill it. So here it is, free for you to judge as pleased! I hope you enjoy!!

**I**

Sam remembers when he first thought about it, how it had felt both physically and mentally, how liberating it had been to finally let himself fantasize about it, to stop burying it as a filthy secret in his own head.

John had been working a case with Caleb - a hunting buddy of his - and left his boys in the town over from it. _“I don’t want you boys anywhere near this beast, it's a nasty one!”_ His father had said about the young werewolf he’d been hunting. Sam had rolled his eyes and answered with a “yes sir” just as Dean had. Sam knew he’d be stuck doing the research. 

St. Paul, Virginia, that’s where he first thought about actually _doing_ it.

It was later in the afternoon, school had been let out for a couple of hours already. He was sixteen and on his way home. Dad had taken the car, but the motel they were at was less than a mile from the small school. He was walking down the small town’s main street, _if that’s what you can call it,_ Sam thought sarcastically as he walked by one of three larger stores the town owned.

This particular store had a display case. As summer was right around the corner - school let out in three weeks - they had their summer clothes on display. The male manikin had khaki shorts, a thin t-shirt, and sunglasses. It wasn’t the male manikin that caught Sam’s eye, but the female one.

Its “skin” was plain white, it, too, had sunglasses on and some thin, silver bracelets on its left wrist. It was the dress that caught and kept Sam’s attention. The particular article of clothing looked like it was in two pieces but it was connected in the front. The skirt was knee-length, thin but thick enough to not be see-through, which Sam enjoyed. The top part was thin-strapped, whit and hugged the manikin in ways that Sam thought could show some glorious skin. The skirt was a flowing mix of light blues and pinks with white as its base. 

The [ dress ](https://only-useless-fanfictions.tumblr.com/image/186005531987) was pretty. Sam’s initial thought. However, not in the pretty-on-another-woman's-body kind of way, but in the oh-that-would-look-good-on-me sort of way. He wasn’t too surprised by it. He’s always liked the idea of dresses and flowing skirts, they just seemed so freeing. This was the first time he’d looked at a dress and pictured it on himself, though. 

Sam was in between growth spurts now, so he was tall and skinny, with wider hips and nice legs. He honest-to-God thought the dress would cling to his slightly curly figure perfectly, making his waist look thinner, and his ass better. The top part would show off his skin, but he didn’t think he was “glorious” at all. The dress was, for sure.

For the longest time, Sam stood there, thinking about how good the dress would look on him, staring dumbly at the display case, standing in the middle of the sidewalk. He even moved his hips back and forth a couple of times, imagining what the light skirt would feel like brushing along his lower thighs instead of the scratchy denim that rubbed at his inner legs and bunched up against his balls when he sat down. He stopped moving like that after a little bit when he realized what he was doing. 

Then he thought of Dean and his father, and he thought of what they would think, 

(“The fuck do you think you are wearing!“)

his blush was immediate and cover most of his neck and cheeks. 

(You will take that pussy, girly shit off right the fuck now!”)

He ducked his head and walked the rest of the way home. He tried to clear his mind before he got back to the motel room, but he was very unsuccessful. He hadn’t been able to stop thinking about it for the rest of the night.

**II**

Now, almost a year and billions of fantasies later, he was actually _planning_ to put on girls’ clothes for the first time. Excitement and nervousness battled to be the top emotion to pour through his body and make his hands shake. 

_What if he got caught? What if he got thrown away like a piece of trash. What if? What if? What if?_ He takes a deep breath to calm himself down, rethinking over everything that he’s done to prepare himself.

Over the last month, Sam has been gathering other pieces so that when he finished putting the outfit together he could try it on. The first was a bra - which he thought would be the most difficult along with the underwear and dress - had been coincidental that he got it. Dean thought Sam was out of the motel room when he brought a girl home. Yes, Sam had to listen to Dean have disgusting sex

(He enjoyed it.)

and wait until after they both finished

(After he finished jerking off to it.)

before he snuck into Dean’s bedroom when they were sleeping and grabbed the bra. He was back in bed and “sleeping” only minutes later. Did he feel bad about taking it? A little, but the joy he felt when he pulled it out from the bottom of his duffle bag the next morning and held the small cups up to his naked chest before his shower had wiped what little guilt he’d felt. 

Then it was a tube of lip gloss he overheard a few girls talking about at school. Sam remembered the brand from the girls at school talking about it and he wanted to snag it from the store’s shelf where he’d seen it. Dean had been with him, so he knocked into the display, discreetly shoved one in his front pocket and had enough time to act embarrassed by Dean teasing him for his clumsiness.

Of course, he hid this stuff in the bottom of his duffle, under all of his dirty underwear and hid the lip gloss - and the mascara that he picked up from a girl who’d dropped it, he’d just _happen_ to forget to give it back - folded up in pairs of his socks. It was a good thing he was on laundry duty for the time being.

Now he was planning on getting the biggest, and final, piece to his outfit.

He was over at Stacy Nove’s house on a study date. She was a year older than him and she needed help in shared Algebra II class. He’s been over for two hours and all they’ve done was math - not that he was expecting anything else despite Dean’s annoying voice in his head talking about how girls only wanted one thing when they invite you to their house after school. 

_And it’s not your_ upstairs _brain, Sammy,_ his brother had said. Too bad for Dean that his brother wasn’t into girls as much as he himself wasn’t into men. 

Sam wasn’t interested. It didn’t even have to do with him not being into girls - he’s pretty sure if there was a _really_ good pair of boobs shoved in his jeans he’d still chub up - and not that he was into guys, either. Maybe he was into both genders? Sam wasn’t sure if he was being honest, his lack of experience didn’t really help matters either. 

One thing he was sure on was that his interest in _one_ guy wasn’t even completely sexual despite his puberty-fresh mind. He was _in love_ with Dean. Dean was the only constant thing in his life and Sam has been looking up to his brother since he could pick up his own head. Dean has been there for him every step of the way, through all of Sam’s life. Was it really that hard to think that the line of _loving_ Dean and being _in love_ with Dean could have gotten so blurry? 

Sam pushed those thoughts away, they hurt too much. Those were the thoughts he left for when Dean and John took off to go on a hunt and Sam couldn’t sleep at night because worry gnawed at his stomach and kept his eyelids open. Those were his 3 am thoughts.

He focussed on the task at hand, waiting for Stacy’s steps to fade as she walked down the hallway towards the bathroom before he jumped up and pulled the door to her closet open. The door opened with a loud creak and Sam held his breath for a moment, when the sound of her returning footsteps didn’t return, he sighed in relief. She had just gotten up to use the bathroom that was downstairs so she wouldn’t be gone for long.

The clothes were hung up orderly, and he took a moment to appreciate that before he rifled through them for a bit before grabbing a purple dress with some lace. He quietly shut the closet door and moved over to his bag. He lifted the books that we're still in his bag and shoved the dress down until it was no longer visible.

He still didn't hear her, so he looked through her drawers for a pair of soft black underwear. He didn't care about her missing them, they weren't going to be in this town for very much longer. As something extra he grabbed a few tubes of makeup and a bottle of what he thought was perfume and stashed those both in his backpack. Zipping up his bag, knowing those things were hiding in there, gave him such a thrill. Sam thought he was high for a few seconds. 

He dove for the bed and started scribbling in his notebook just as the door creaked back open. She smiled down at him and he realized with a shock that she had a different, more revealing top on.

"Hey, Sam..," she said sweetly and walked over to the bed.

Sam, oblivious to her obvious outfit change, he looked up at her and asked what she wanted.

"Nothing.." she dragged out the word as she lent down to see what he was writing, showing off her cleavage to him. His eyes stuck for a second, mesmerized by the shape of her breast, and how it stayed in the cup of her bra. 

When she leaned in even more, he moved away from her. He pretended that he didn’t see the hurt look that flashed on her face. She motioned for him to scoot over on the twin-size bed and he did so, as so to not hurt her again. He didn’t know how to tell her that he wasn’t interested, especially after she caught him looking down her shirt.

Sam moved over and she did what he hoped she would not: she moved and laid down next to him. He leaned the opposite way so their bodies weren’t touching, after a moment, she leaned into him. His shoulder and hip were pressed into her, her leg pressing up against his. 

“Hi..,” she whispered when he met her gaze. Their faces were really close and Sam had to push down the urge to get up and move. He didn’t want to give her the wrong impression, being led on was a horrible feeling and he wished to never do that to someone else. 

And still, he smiled at her because she did look nice in that top and she did sit in a way that pushed her boobs up. Sam caught himself looked at her chest for a moment too long and when he looked back at her face, she was grinning. Sam’s heart fell when he realized she thought he was interested in her. 

“Stacy, listen..” he trailed off, his tongue growing dry in his mouth. 

Something in his tone must have given him away, “What?” She sounded a little annoyed and she leaned back to really look at him. Sam suppressed a sigh in relief. “You don’t wanna mess around or anything?” 

“No, not at all!” he immediately blurted out. As soon as the words were out, he wanted to beat himself for his stupidity. That was completely opposite of what he should have said. Now he had to come up with some lie to spare her feelings and confusion. 

“Well?” her eyebrows reached for her hairline. 

“My mouth is dry,” Sam mumbled. “Uh- Can you go get me some wa- a soda, maybe?” Sam hated lying and he kind of sucked at it too. 

“You want something to drink?” She asked in slight disbelief. 

Sam nodded, hoping that she would get up and get him one. Just for the sake of moving away from him. Her touch made him a little uncomfortable. She nodded and stood up, taking a second to do so. 

Sam watched her walk to the door, but he did not watch her the way a man watches a woman. He didn’t watch her and grin or bite his lip. He didn’t watch her and think of all the ways she could please him. 

Yes, he watched the way her hips swayed left and right. He watched the way her feet crossed in front of her as she took each step. The way her jeans clung to her butt and the shirt to her boobs, the roundness in both. He watched the way her hair swished back and forth across her shoulders. He did this every time he watched a girl move. 

He studied them. He watched so many girls of all shapes and sizes, in the way they sat, in the way they walked or jogged, in the way they _existed_. He’d watch and wait. Wait until he was alone in an empty motel room and practice doing the things he’d seen.

“Yeah, okay,” she grinned, pulling Sam from his thoughts. “I’ll go get you that drink.” She left with a twirl of her hair and Sam jumped up the moment she was gone. 

He gathered his notebook and Algebra textbook and threw them in the bed, the thudding sound muffled from the bundled up dress. Once his stuff was around and he slung his bag back onto his back, he looked around for an excuse to leave. When Stacy came back she was going to want to mess around with him and he wanted no part of it. 

“Shit, shit, shit,” he mumbled as his head whipped back and forth. The only thing he could think of was to go out the window. She was on the second floor, but there was the wrap around porch’s roof right under her window and a grand oak tree that was perfect for climbing up and down. Stacy herself had told him and her group of friends that she snuck in and out of her window like that. 

Was he really going to skip out on this girl? Sam sighed and considered it, moving closer to the door. Sam thought about how much longer they were going to be in this nothing town, it wasn’t much longer.

“Sam!” Stacy called up from what sounded like the other end of the house where the kitchen was. Sam jumped at the sound of her voice. “Coke or Dr. Pepper?!” 

“Uhh…” Sam shouted back. “A Coke is fine!”

Sam went over to the window and unlocked it. The ledge was clean when he grabbed it and heaved the window open. The wind that moved the tree’s leaves around with ease blew in and Sam smelt a campfire. The smell calmed his rising panic. He’s never done anything like this, he’s never skipped out on someone and Sam didn’t realize it would make him feel so bad. 

Stacy’s steps could be heard coming back, which made Sam’s decision for him. 

He shut the window behind him and didn’t look back. 

**III**

Back at the motel room, Dean was surprised to see his brother back so soon. At first, he didn’t say anything and Sam was grateful, albeit a bit wary. Sam knew Dean like the inside of his hand, there was no way Dean didn’t want to nail Sam with question after question. For now, though, they just sat on the matted, stained up couch and Dean flicked through the six different channels this motel had to offer. 

"So, how was it?" Dean asked after a while.

"How was what?" Sam stared at the TV, unflinching at the feeling of Dean’s gaze that was on him. He pretended to be really invested in the commercial for some thyroid medicine that was playing on the small TV. 

"Hanging out with a girl all by yourself for the first time,” Dean said. “Ever," he tagged on at the end. The way he said it, Sam knew he was still sniggering about it. Yeah, so what if Sam was 16 and it was the first time alone with a girl? That didn’t mean anything. 

Sam focused back on the small screen, squinting to read the small text of side effects at the bottom. _“It really cleared up my symptoms in days!”_ The lady holding the small pink bottle cheered with a smile. The narrator’s voice was back, he was saying, “ _Get your own bottle and clear mind today! Just call the number at the bottom of your screen or go to www.nes-”_

The TV screen blinked out. Sam looked over at Dean who was bringing the remote back down from where he had raised it to get the button to work. Dean smirked and met his little brother’s eyes. Sam blushed then, his face always heated up when he looked at Dean straight on for too long. 

"Umm…” Sam fought with pushing his thoughts back, sealing them up in the foolproof container in the back of his mind where _those_ thoughts are supposed to be. “It was just like hanging out… with uh.. a dude.” Sam rubbed the back of his neck, unsure of what to say. “I guess,” he added at the end. 

Dean looked at him with a face of true shock. "You mean to tell me, little brother,” Dean said. He scooted closer to Sam on the couch. Sam wanted to back away because he could feel Dean’s breath blow onto his face and could smell the _Funyuns_ he must have eaten earlier and still, Sam wanted to kiss him. “You didn't try anything?"

“Uhh…” Sam tried to look away, hell, he even tried to move away, but Dean’s stare has him pinned right where he was. Sam had been watching Dean’s mouth move as he talked, less than a foot away from Sam. Now his gaze moved up and counted freckles as he took a minute to collect himself. “No, I didn’t, Dean.” 

“Sammy…” Dean whispered. He leaned in a little bit closer and Sam’s heart stuttered before picking up on speed. Was Dean about to kiss him right now? What the fuck? Hold shit, what the- “Why not!?!” Dean _screamed_ in his face. 

The force and sheer volume alone made Sam jerk back. Dean scooted back laughing, keeping his arm raised in case Sam slugged him. Too bad the boy was too winded to do much besides frown at his older brother. A few moments passed and Dean stood up, walking a few paces back to the kitchen to get a glass from the clean sink. 

“Come on, Sam,” Dean said after he didn’t get an answer after a while. “It was a serious question.”

 _Sorry, Sam is not home right now._ The teenage boy thought bitterly. _Sam’s brain has short-circuited because for a fucking moment he thought his own damn brother was going to_ kiss _him and so now his brain has spontaneously combusted. Leave a message at the tone and Sam can get back with you as soon as possible._

Sam inhaled deeply and closed his eyes for a moment. His heart started to slow down and he was able to think straight again. God damn, Sam has never felt like that before. He _actually_ thought Dean was going to kiss him and that would have been… a lot of things. 

“Because,” Sam said, turning around on the couch to look at Dean on the other side of the room. When he did so, he noticed a little something that he hadn’t before. He was hard. In his jeans. Sitting on the couch less than five feet from Dean. 

“Because?” Dean prompted.

“I don’t know!” Sam cried, a little stressed and worried about how he was going to get around his brother without the older one knowing about his little - big - problem. “I just wasn’t into her, I really thought she just wanted help on her homework…” That was the truth. 

“Oh, Samuel..” Dean cackled. 

“Shut up,” Sam muttered before the other boy could get anymore teasing out. 

Dean put his hands in the air in an ‘I surrender’ gesture. “Hey now,” he said. “I’m not going to say anything other than I tried to warn ya! Girls only want one thing from you.” Dean winked at him and Sam’s throat constricted on itself. 

Dean walked past Sam, hitting him on the shoulder as he passed, and disappeared into the bathroom. Moments later Sam heard him start to relieve himself in there so Sam sat on the couch normally and reached for the remote, ignoring the throbbing in his groin. He turned the TV on to drown out the sound of his brother pissing and to distract himself from his semi. 

That was when Sam remembered the dress at the bottom of his school bag and his heart fluttered for a whole new reason. 

**IV**

Sam wanted to wait until the next hunt Dad took Dean on. That way Sam would be completely by himself for at least overnight and he could be able to try on the damn dress. Except, it’s been _weeks_ and Dad hasn’t taken Dean on a hunt with him. Right now the two boys were stuck in yet another motel room somewhere near the northern Texas-New Mexico border. 

It was later in the afternoon in the middle of April so the temperature wasn’t the burning hot of summer but it was still a little warm. And their AC was out, so Sam felt like he was dying. 

Dean walking around in just his underwear had nothing to do with Sam dying either. 

“Fuck me,” Dean says loudly, sitting in one of the metal folding chairs that went with the old card table. This was one of the motel rooms on the poorer side of the scale. “It’s so hot!”

Sam tenses his shoulders and refuses to look over at his brother, he already knows what he’ll see. Instead, he replays Dean’s _fuck me_ over and over in his head. Sam’s been turned on since Dean took his shorts off a little over half an hour ago. It heats him up more, his warm arousal pooling low in his gut and making him wanna rock back and forth to get some friction in his groin.

“It’s not _that_ bad,” Sam muttered, unsure if Dean even heard him. 

“Not that bad?” Dean echoes. Sam hears his older brother get up from the chair and he curses to himself. “Sammy,” Dean says right behind him. Sam shuddered when he felt the other’s breath ghost over his neck, God, now his nipples were tightening and Sam wanted to arch his back and present his ass, repeating what Dean said moments ago. 

“Yes, Dean?” Sam leaned more into the back of the couch, getting a little closer to Dean he knew, to pull his legs up so he could hug his knees. He didn’t know what else he could do to hide his erection, but fuck Dean, okay? How dare he have this stupid power of Sam and not even realize it. 

“It’s hot as balls out right now. I literally have sweat dripping down my ass crack-” That shouldn’t be sexy at all, but good Lord Sam’s cock twitches and the boy squeezes his legs tight. His arousal is cranked up now, there’s no way his hard on will go away on its own. All he can think about is peeling Dean’s underwear back and _licking_ the sweat off his body. Shit, how many kinks did Sam have? “-so don’t tell me it isn’t _hot as fuck out right now_.” 

The last part was whispered directly in his ear. Dean had pressed his lips to Sam’s left ear and the teenager had a mini seizure because of it. Fuck, his orgasm went from zero to sixty in three seconds flat. Sam did arch is back then, but disguised it as shifting around on the couch.

“Yeah,” Sam mumbled, turning his head. “You’re right… It’s hot out.” He met eyes with Dean for a split second, but he got distracted by a drop of sweat running down his temple. Dammit, Sam wanted to run his tongue up the side of his brother’s face to catch it and he wanted to wrap his arms around Dean’s shoulders and wind his legs around Dean’s hips so that he can cling to his brother and grind his aching cock against-

Sam felt a sudden pain in the back of his head and his neck bent forward with the force behind Dean’s hand when he hit Sam. The younger brother didn’t even feel the pain, but he heard Dean’s laughter when the older one stood up and walked away. 

“Damn right, I’m right.” Dean’s laughter followed him to the other end of the room. Sam turned back to the TV feeling like he was in the same motel room as always. The setups were always the same. 

Sam didn’t say anything. He did release his legs from his arms and looked at the bulge in the front of his gym shorts. He glared at it like it had done him wrong by standing up. 

“Hey, Sam…” Dean said. 

Sam paused waiting for his brother to continue. He said, “Yes?” when Dean didn’t. 

“How likely to tell dad are you if I leave?” _Please do,_ Sam begged in his own head. Sam loved his brother, but right now he desperately needed to get a hand on his cock and he couldn’t do that with Dean here. 

Sam turned his head and looked at his brother. Dean was standing next to the sink, leaning on hip into it, and pouring himself a glass of water. His older brother wasn’t looking at Sam. “Yeah, I won’t tell.” 

Sam knew why Dean wanted to leave. Dean has been stuck with his brother for the last four days and Sam knew the signs when Dean was getting horny. He was more irritable, he took longer showers, and liked to tease Sam more. Which is everything he’s been doing as of recently. Sam knew that Dean wanted to go find a girl to stay with. And the 16-year-old boy was willing to keep it from dad as he had every time. 

“Really? Sweet!” Dean put the cup down and walked over to his duffle, grabbing a fresh pair of jeans and a t-shirt. 

“How uhh…” Sam scratched his hair and pulled up his legs again when Dean walked around the front of the couch to get to his bag. “How long will you be gone?” 

Dean looked up and smirked, “Probably all night.” Dean wiggled his eyebrows at Sam.

Sam nodded. That could work.. Sam would have the night to himself (finally) and he could ease some of his own tensions. Maybe even try out some of the new clothes that have been burning a hole in the bottom of his bag.

“Okay, I’m going to shower and leave. Have fun with yourself, Sammy!” Sam watched in horror as Dean made a pointed look down to where he's pulled up legs were covering his crotch. Dean grinned at his brother and winked again before bursting out in laughter before heading to the bathroom.

Dean knew he was hard, didn’t he? If so, how was he okay with it? Maybe he didn’t know that he had been the cause of it? Yeah, Dean was 16 once, he knew life was ruled by boners and pimples. It was fine, Sam took a deep breath to calm himself down. 

Despite his freaking out, his hard-on didn’t even waver. 

The bathroom door shut and a second later Sam heard the shower start. Dean seemed happy to be leaving, he knew that feeling cooped up has never been Dean’s forte. He’s glad to see his brother happy, but he’s also upset that Sam couldn’t supply that happiness. Sam brushed that aside, too used to thinking about his jealousy later and not at the moment. 

Sam waited a full minute later (he counted) to make sure Dean was in the shower. Then he slowly reached a hand inside his shorts to run his fingertips up the shaft of his dick. It made hi hips jump from the electric shock of pleasure to hit him. His other hand came up to use his index finger to rub around his nipples that never softened. 

A small groan escaped the teenager when he wrapped his whole hand around himself. _Fuck me_ Sam heard Dean shout again, except this time it wasn’t in frustration from the heat, it was moaned out. 

“Oh, God…” Sam whispered, moving his hand faster. Sam has always enjoyed a hand on him, one that could cup his entire dick and rub hard and fast but also enjoyable and soft. 

Precome globbed out the swollen and, no doubt, red tip. The shorts were baggy enough that even fully erect, his dick stayed hidden by them. Sam didn’t need to see, though, he knew his own dick by heart. 

He thumbed at the head to collect some of the liquid there to spread across his palm to make the glide easier. _Fuck me!_ Dean in his head again screamed. Sam arched his back and pressed his cock hard into the seat of the couch through his shorts. Fuck, he didn’t think that would feel so good. Sam rolled his hips and that created deliciously rough friction on himself so he did it again, hips jerking quickly. 

His left hand came up to cover his left hand to muffle the little whines that wanted to slip through. God, he really needed this. Fuck, it felt so good. 

Sam looked up and to the bathroom door, it remained closed and he could hear the shower still running, but he let his mind wander. What if he went into the bathroom now? What if he just dropped his clothes and got into the shower with Dean right now, hard prick and everything. 

Sam arched his back so far his neck strained itself trying to throw his head back far. He was close, holy shit he was close. Pleasure zinged through his body as his hips picked up their speed. 

Would Dean freak out? (probably) Not in his fantasy he didn’t. Instead, the Sam inside his head turned Dean around and dropped to his knees. Dean’s cock - hard, flushed, and beautiful - was right there in his face and Sam nuzzled it, letting the pre-come at the tip smear against his cheek and rub into his hair. Dean’s hand came down and tangled his hand in Sam’s not-wet-yet hair and pulled him where he wanted, with the head of his dick poking past Sam’s lips. 

The hand covering Sam’s mouth moved and he poking his first two fingers in past his lips. The rough feeling of his teeth against the pads of his fingers triggered a massive pleasure that made him roll his hips. The couch had a small plastic border wrapped in the fabric around the edges of the cushions. The plastic scraped against the slit on the top of Sam’s dick and the boy was close enough that that was what throw him over the edge. 

Sam’s hips never stopped moving and his hand squeezed him to milk himself of all he had. Sam pulled in the air roughly through his nose and panted out his mouth. He pulled his sticky fingers from his mouth and his other, more messy, hand from his shorts. 

“Fuck,” he cursed, looking down at the dark spot on the front of his shorts. Well, now he had to change and he was sure Dean would notice. But there was no way he could stay in these, his cooling come was already sticking the material of the shorts to his softening dick. 

Sam got up - using his elbows to support himself so he didn’t smear cum or spit anywhere - and went to the kitchen sink. It was gross to wash his hands here, yes, but he and Dean didn’t cook anything anyway. 

Once the mess was cleaned from his fingers, he stopped and listened to the sounds coming from the bathroom. The shower was on for the moment and so Sam darted over to his duffle. He opened it and pulled out a clean pair of shorts from the bottom. A piece of the burgundy-colored dress poked through and Sam was quick to shove it back down. He looked over his shoulder as if Dad or Dean were suddenly standing there staring at him with disapproval. Sam straightened up and pushed the dirtied shorts from his hips to change. 

That’s when he heard the shower shut off. Dean was going to get his dick wet, of course, he wouldn’t be in the shower for long. Sam cursed to himself and pulled the new shorts on quickly, completely forgetting about underwear. Before they were up all of the way, Sam took the old pair’s cleanest side and wiped himself down. Then he threw the nasty pair in his duffle and sipped it back up. 

Sam dove to the couch and had the remote in his hand when the bathroom door opened up again. The younger boy’s heart was pounding while he was pretending to be calm and not care about what his brother was doing. In reality, he was freaking out and barely even seeing the TV. 

Also, what the fuck was that fantasy? Sam’s never thought of Dean manhandling him like that. He’s never thought that getting his hair pulled would actually feel good but holy fuck had that been hot. Even so soon after an orgasm his stomach jerked with fresh arousal at the idea of Dean just grabbing Sam’s face and hair and _forcing_ him to take his-

“Whatcha watch’n, Sammy?” Dean shouted, suddenly yelling right behind him. 

Sam jumped and whipped around to glare at his brother but he was gone. Sam sat up on the couch and saw that Dean was putting his shoes on by the door. Dean met his eyes and laughed, “new shorts, aye?” Then he pulled the door open and slammed it shut behind him. 

Sam stared at the door in disbelief before sighing and falling back onto the couch. 

**V**

A few hours later and Sam was itching to try those clothes on. He’d sat around for a while by himself, he read a little bit of his beat-up copy of _the Call of the Wild_ and eventually got bored with it. The TV only had seven channels this time, one of _Sesame Street,_ another of an old Clint Eastwood movie that he knew Dean would want to watch, and a couple more channels playing stuff that bored him. 

So now here he was with his duffle open and [ the dress ](https://66.media.tumblr.com/c3bb2a498f121512e3309cb4558765e2/tumblr_pu10c0avgQ1yqbw60o1_500.jpg)in his hands. It was a deep red or burgundy color. It was thin-waisted 

(would it even fit him?)

and short. When he held it up to himself, it only went to mid-thigh. The thought of whether or not it would fit him sent a thrill through Sam because he knew the only way to see if it would was to _try it on_. 

But something stopped him, maybe it was the risk of his brother or father walking in on him. Or maybe it was just him not wanting to take it that far. What would happen if he tried it on and found he absolutely hated it? Sam enjoyed jerking off to the _idea_ of wearing women’s clothing, but what if he really hated the idea of _actually_ wearing it and that ruined the fantasies? 

"Isn't this the reason you stole the clothes in the first place?" Sam rationalized with himself.

With a loud and dramatic sigh, he grabbed tightly onto the dress and gathered it up with the duffle bag. It had the rest of the clothes in here and he wanted to see what it felt like the wear women’s undergarments as well. Well.. would he take it that far the first time? For now, he just wanted to try the dress on.

He closed the bathroom door behind him and listened for the loud click to echo off the walls. He set the bag down and felt around for the light switch. The sound of his hand scraping across the wall was almost deafening in the otherwise quiet room. The light switch was flicked up as soon as he felt it and the room was washed in bright, white light. The light fixture and bulb must have just been recently replaced because it didn’t flicker or dim after he turned it on. 

This bathroom was small with cream-colored walls. When you walked in, the shower with its plain white shower curtain was on the opposite wall, and on the left-hand side was the toilet. Immediately after the toilet, the closest thing to the door was the sink and small set of drawers and cabinets. 

Above the sink and extending for a few feet was a mirror. This mirror only showed Sam from the chest up. There was a longer, full-body-length mirror attached to the back of the door. This is the one that Sam turns to and stares at himself. 

How many times has he stared at himself in a mirror like this? How many motel rooms? How many mirrors? Sam did not know any answer except for _all of them_. 

Sam has never really hated his body before, of all the times he stared at himself with a blank expression it was never disgust that he thought of. He never looked at himself and thought his body was gross. 

As of recently, he’s felt that his body was _missing_ something. 

Sam took off his shirt and looked at his flat chest. He looked at his flat, boobless chest and tiny nipples. Would he really want to get boobs put on? Probably not. This is where his head gets really confused because he does want to have a little extra cushion on his pecs because he likes the way they look on girls. 

But Sam really liked his penis, too. He liked that he was a guy, he did. He liked his flat waist and thick shoulders, he liked his narrow hips and long dick. It’s not that he wanted to _be_ a woman. He just… he didn’t know. 

“It’s just confusing…” Sam mumbled to himself. He had to look away or he would continue to stare at his reflection until he got tired or Dean got home the next morning. 

The excitement that crashed through him like an angry bull crashing through an old, wooden fence, woke him up and made his hands shake. He picked up the dress again and held it up to himself, attempting to line the shoulders of the dress to his own. He then looked back at the mirror. 

His breath caught in his throat. He didn’t even have the dress on and he knew that it was going to look great on him. His eyes teared up and he got a little angry at his own reaction. He dropped the dress and scrubbed at his eyes. _I think I’m excited enough to actually be crying. Oh man, I didn’t know I would like this so much…_

Sam dropped his shorts and picked up the dress again. For one second he stopped and listened out into the main part of the motel room. He just wanted to make sure that Dean and Dad were really gone. But yes, it’s been three hours since Dean left and it was almost 11 o’clock at night so Dean is definitely staying the night at whoever’s house he went to. 

Sam unzipped the dress in the back and slipped it over his head. It was a little rough around the edges, but the inside was mainly soft. It fit easily over his head and shoulders. It bunched up a little under his arms and so he had to awkwardly reach up and pull it down. He panicked for a split second when he couldn’t get it down all of the way because what if he couldn’t get it off by himself and needed someone’s help? He pictured Dean and Dad helping him take the dress of and how Dean would laugh at him and Dad wouldn’t be able to meet his eyes. 

Sam shuddered and brushed the thought away. Especially when he got the dress pulled down where it was supposed to be. Then he looked up in the mirror. 

“Oh, shit.,” he whispered. 

Sam smiled at himself, he didn't think he was going to fit in this dress. In the last couple of weeks, while he was getting these clothes around, he kept sneaking pictures off the internet while researching. At the time, Sam had done his research in a library away from his brother and father. The first time he’d looked up a picture of a man in a dress he had been disappointed. The nonexistent waist and flat chest had definitely not flattered the dress. The bitter disappointment had put him in such a funk that even Dean commented on it, of course, Sam threw him some bullshit excuse. Two days later, he was over at Stacy’s house. 

In this dress, though, he _had_ a curvy waist, he had a butt, and he had a thick chest. It came with pads around the chest area, so it looked like he actually had - rather small - breasts. The size didn’t matter, he just liked the roundness there. He turned to the side and sucked in his already flat stomach to puff his chest up. Yes, they looked real there. 

He gave a small twirl and laughed at himself in the mirror. He couldn’t believe that it fit so good. He twirled again, losing his balance for a second and crashed into the counter. Sam didn’t care though, all that mattered was the skirt of the dress had puffed out and floated down to his thighs again. 

He cocked his hip to the side - which made him look even better - and he felt the soft and rough fabric rub against his legs. The outside lace of the dress that was folded around the hem and sewn in had caught a little bit on the hair on his legs. It was a tantalizing feeling and he moved the other way. Back and forth he rocked his hips and turned sideways again, this time looking at how this dress curved around his ass. 

“I didn’t know it was that big…” he mumbled to himself.

He tensed and stood up on his tiptoes and watched his legs. The muscles hiding under the skin of his calves and thighs tensed up and held. He grabbed the wall beside him to balance himself and wondered what it would be like to wear high heels. Goddamn, his legs would look good in heels. 

Sam dropped back down to his heal and turned to look at himself head-on. His eyes ran over the sturdiness in his legs, the curves of his hips up to his waist, the small swells on his chest and his thin neck. The dress’s collar ended right on his collarbone and he got just a glimpse of the strong bone there. 

Then he looked at his face. 

He looked at his long face, his thinner-than-most-guys’ eyebrows, his prominent cheekbones. His eyes are what really drew him in. Sam stepped closer to the mirror, ignoring the smudges and little white dots that were in some areas of the mirror and really _looked_. Not once in the last couple of years has he looked in the mirror and saw his eyes shine like this. 

It was the shine that you read about in books and saw edited in movies. It was the shine that shone back at him and made him feel light. He may have imagined it, but when he smiled, did his teeth sparkle too? _Of course not, you idiot,_ Sam thought. 

He looked up this close and saw blackheads on his nose. He saw bags under his eyes and messy hair. He saw a small mouth and a long chin. He looked father away and saw scrawny arms and a thin neck. Usually - when he dressed in jeans or shorts and a t-shirt - he saw all of these things as wrong. 

(Okay, maybe the blackheads and bags under his eyes weren’t _actually_ attractive)

Now Sam just _didn’t care_ . He looked at his body and did not care about the blackheads or the bags. He didn’t care about these imperfections because the things that bothered him before - the scrawniness and thin waist, his high cheekbones and long eyelashes - looked... _good_. The dress clung to him and made him feel pretty. 

He backed away from the mirror enough to get a full-body glimpse. His hands came down and slid up his sides and then down his front. He came up to his chest and his hands felt around there, feeling the padding of the bra but also the extra room that was there. He turned to the side and looked at himself that way, seeing the extra room there. 

Sam grinned mischievously and grabbed a big chunk of toilet paper. He knew that some girls got ridiculed for their bras to make their boobs look bigger, but considering he didn’t have any boobs at all he felt it would be all right. He shoved the even handfuls of toilet paper on each side of the dress and it puffed his chest out again. Now they looked fuller and he turned from side to side, the grin on his face turning into a full-blown smile. 

Sam couldn’t believe how happy he was right now. It was bursting at the seams, he felt lighter and freer. He twirled again in the mirror and felt like he could exist like this. He never wanted this to end. He deserves this euphoria. 

Sam opened the bathroom door and walked into the main part of the motel room. He had made sure the curtains were closed by peeking out the door before he went. He walked with a bounce in his step and his chin up high. 

_What would it be to just_ wear _this every day?_ Maybe not this exact dress, but to just wear a dress every day. Sam spun on his toes - he was off-balanced from not used to being on his toes much - out here where it was more open and he could spin for longer. 

When he slowed down he wondered what it would be like to wear _nothing_ but the dress. With a sly grin, he reached under the skirt and after looking over his shoulder to the still empty room, he dropped his underwear and kicked them to the side. Immediately, there was a lot of airflow down there and it gave him goosebumps. His balls jerked when he spun, the air new was very pleasant because it wasn’t cold air because it was still hot out. 

He ran a hand up to his inner thigh and under the skirt again. His index finger rubbed at his tender balls and it made his cock jump. Arousal has been pooling lowly in his stomach since he first looked in the mirror and now the warmth traveled to his cock as it hardened. 

“Fuck…” Sam sighed and gripped himself tighter. 

Thank fuck for being a teenager, Sam laughed at himself as he slowly starts moving his hand. He’d just gotten off earlier but, fuck he hadn’t felt like this. _It’s because it’s new,_ he thought. _You’ve gotten off to thoughts of big brother so much, but this? Jerk’n it in a dress was new._

Sam spread his legs and his other hand went down to touch his balls again. Sam thumbed at his slit and it made his hips jerked forward, he panted loudly and moved his hand faster. He didn’t want to get his spunk on the dress because he had no way of cleaning it so he’d take it off before he came. Man, this felt so good. 

Sam reached his hand from his balls to around his leg and brought it behind him. He’s never actually been brave enough to finger himself - whether it was the idea of finally doing it or the possibility of getting shit on himself he wasn’t sure. For now, he rubs a dry finger over his pucker and moans at the feeling. 

Then the motel front door opened. 

Sam gasped a looked up at the door, the light from the neon sign outside lit up the parking lot enough to shine more light inside. Sam didn’t move as whoever was coming in closed the door and walked around to see Sam standing there. 

“Sam?” Dean gasped. 

The older boy stood there for a few seconds, looking Sam up and down. Sam wondered what kind of sight he was standing there in the middle of the room, wearing a dress, holding his dick - now completely and pathetically flaccid - in his hand and a terrified look on his face. He was the very embodiment of a deer in headlights. 

Sam didn’t answer Dean, but his reaction was to tense up and squeezed his hands shut, which would be fine, especially for the hand that had been touching his entrance because that arm shot forward when the door open. However, the hand around his dick didn’t move and he squeezed his appendage harshly. The pain grounded him in a weird way and caused him to whine loudly. 

Sam watched his brother looked down at his crotch and a worried expression fall onto his face. “Sammy,” he said, his voice was rough and scratchy. “Let go, you are going to hurt yourself.” 

Dean stepped forward and Sam jerked back. The teenager’s foot slipped on his previously discarded underwear and he went down. The skirt of the dress flipped up and his hand finally released his abused dick to catch himself before he fell completely back. His mouth opened to say something, anything but instead, he only cried out. 

Dean looked around in a panic, Sam could see he didn’t know how to handle this situation. “I..” Dean started but stopped. 

Sam began to get some feeling back into limbs and until that happened he hadn’t even realized how paralyzed he’d been. He also realized how exposed he was with the skirt flipped up and quickly jumped up to correct that. The younger boy saw that the bathroom door was still open and he risked a glance at his brother who was still standing there dumbfounded. 

Sam saw his chance and took it. He darted past Dean, who didn’t have enough time to fully turn before the bathroom door was slamming shut and the lock clicking. 

As soon as the door was shut, as soon as there was a barrier between him and Dean, Sam broke. His knees buckled and he dropped to the floor. His head hit the doorknob on the way down and his ear had taken most of the pain, the skin and cartilage now red and tender. The tears came full force then. 

Sam brought his legs up and his hands went to his hair. Hard, forceful sobs rocked his body and shook his core. He could even believe-

How had he been so _fucking stupid_ ? Why had he thought it was a good idea to prance around the room like that? And oh God, when Sam fell. He started trembling when he thought about Dean seeing _everything_. He was such a fucking pathetic idiot, such a loser and a disappointment-

“Sam?” came from the other side of the door. He heard a knock above his head that he ignored. 

Sam cried harder. 

Why was he even wearing this? Through the tears he looked down at himself, he looked down and saw the dark red of the fabric and the puffed up chest, filled with toilet paper. Why did he ever think to do this? 

Who even wears this? What guy would _ever_ -

Sam starts jerking his body around and grabs for the collar of the dress. He gets fistfuls of fabric and pulls and yanks at it, trying to get the offending material off of his body. He’s so suddenly and viciously full of anger and resentment at himself that he reacts physically. His elbows and knees knock into the cabinets underneath the sink and into the door; he barely feels it. 

All he wanted right now was to get this dress off. All he wanted was to not be here right now. Sam’s mouth opens and contorts, an ugly sound threatening to come out so he grabs his own neck and chokes off his breath. There’s only the sound of him gagging. 

“Sam!” Dean’s tone rises in panic, he pounds on the door a little harder. 

Sam recognizes that he should answer his brother, instead his frustration and self-hatred builds. He can’t get the stupid fucking dress off and he just wants to not exist anymore. Tears stream down his face and neck, wetting the hand that squeezed harder and felt the tendons in his neck strain and the other scratching at his collar bone trying to tear the dress off. His body shakes with sobs he can’t experience because he isn’t letting himself breath, he isn’t letting himself swallow, he isn’t letting himself do anything but feel the deathly hand around his throat. 

When it becomes too much and he _has_ to breath, he releases his throat and pulls air into his lungs violently. He’s sobbing and talking with a rough voice. “I can’t.. I can’t- ahh!” He grabs at his hair in both hands, yanking and tearing. Sam didn’t want to _fucking exist anymore_. 

“Sammy!” Dean pounds on the door, Sam feels the force of it where he’s leaning against it still, it shakes his skull. “Open this fucking door right now!”

Sam found his voice enough to scream, “No!”

There was a pause

(did he leave?)

before Dean’s voice was back and softer. “Sam,” he begged. “Please, tell me what’s going on?”

Sam shook violently, but he was calming down a little bit, he could feel that much. His sobs weren’t so harsh and there was more breathing between them. It was the worst feeling to Sam, to be crying so hard that you lost control of your body and you were turned into a hard, shaking corpse. Sam was coming down from there with hands still tangled tightly in his hair and was yanking up on his scalp. 

“N-no,” he breathed out. He took a deep breath, released his hair and fatigue waned heavily through him. “Whu-ye are you-ou even here?” Sam asked. His breath shook with no control, it was from crying so hard.

Dean answered right away, “I’m not supposed to be, but then the girl I was with, her dad came home.” 

Sam couldn’t figure out how Dean was dealing right now because the door muffled his voice too much. He was probably doing all he could to hide his disgust. Of all the things Dean could come home to, it’s his _faggot_ brother in a damn dress. Sam hunched forward and grabbed at the back of the dress again, but all of the energy is seeping out of his body so he doesn’t pull very hard. He’s just so tired now.

“Sam, you need to explain this to me…” Dean begs, he must be crouched down or sat down because Sam heard his voice closer. “I- 'm just... confused right now, kiddo.” 

Dean’s gentle voice makes him cry again, Sam cleared his throat and swallowed back the lump in his throat so his stuttering voice could say, “..’ st don’t know huh-ow.” 

There’s a long moment of silence. Dean’s lack of an answer, or anything, settles a heavy, cold stone in the bottom of his stomach. It turns him cold despite the heat that was in the air. His body was still trembling, and now he felt like he was going to throw up. Good thing he was already in the bathroom, he thought humorlessly.

“Can I come in?” 

Sam was giving up, he didn’t want to hide anymore. He slid forward and brought his hand back up and unlocked the door. He took a deep breath and turned towards the door, still sitting on the ground. Sam slid until his back was to the tub, then he said dully, “You can come in…” 

Dean opened the door, the creak was the loudest thing beside Sam’s breath that trembles with his body. And oh, what a sight Sam must be. With his wrinkled dress, bare legs pressed into his chest which barely covered his junk, face red and blotchy, tears still falling, and body possessed by vicious tremors. Sam knew he looked pathetic and, man, Dean must be a good actor because there wasn’t any trace of disgust or disappointment on his face or how he held himself. 

Dean took two steps inside the bathroom (Sam counted them) and crouched down. He reached a hand out to touch his brother’s knee, but Sam flinched away. He drew his hand away and sighed. 

“Sam…” the older brother whispered. “What’s going on?”

Sam was no coward. He’s been on hunts where he’s stared down the growling and snarling beast with no less than a slight chill of fear. Now though, facing his brother felt like the biggest and hardest thing he’s ever had to do. He couldn’t do it, not dressed the way he was. Not as shaky and unsteady as he was. Sam buried his face in his arms that were folded on top of his pulled up knees. 

Sam couldn’t see him, but he heard Dean’s butt fall to the ground and him cross his legs. Dean wasn’t going to leave him alone. That thought made him tremble again and hugged himself tighter. 

Dean was there and he was prepared to be as patient as Sam needed him to be. 

Dean’s silence felt like someone driving an icicle into his side. It stuck there and didn’t budge. Sam wasn’t sure how long they stayed like that, but long enough for Sam’s tears to stop and his trembling to die down to be almost nonexistent. It was only when Sam’s back started to ache from how he was pressing himself into the bathtub that he finally tilted his head to peek up at his brother. 

Dean was there looking at him with raised eyebrows. Sam knew he wanted an explanation, but… the kid just didn’t have one in him. 

“I don’t..” Sam croaked. He stopped to clear his throat, it was raw from the lack of use, crying, and choking himself earlier. When he swallowed, it burned because of his throat being so dry, but he tried again anyway, “I don’t know what you want me to say.” 

Dean looked at Sam for a little longer than the younger thought necessary, before he spoke, “Dude, we all have kinks-”

“You think this is just a-”

Dean held up his hand, Sam stopped. “We all have things that we are into. You’re 16, you’re supposed to be figuring this shit out, man.” 

All Sam could do was shrug, “How many…?” Sam’s voice died and he just couldn’t continue. He knew he was a freak, but did he really want to ask Dean about it? How much did he really know about this kind of stuff? 

Dean scooted a little closer, their legs were almost touching. “‘How many’ what?” he prompted. 

Sam ran a hand threw his hair and straightened his legs. They’d been starting to cramp and him stretching them out felt like the coolest relief. Then when his long legs stretched far enough that his toes brushed up against Dean’s knee, the coolness heated up with a blood blush on his cheeks and neck. He’d just started cooling off. 

Except, Dean didn’t shy away from the touch, or turn away in disgust like Sam thought he might. 

Instead, Dean slowly raises his hand - as if to not spook Sam, which the younger boy appreciated because he had no idea what his brother was doing - and placed it on Sam’s leg. It was his right leg and the bare skin that Dean was touching

(Sam suddenly remembered that he was _only_ wearing the dress)

lit up with a calming heat. Dean’s fingers gently pressed into the muscle there and his whole hand rubbed up and down. He was messaging Sam’s leg. 

“‘S okay?” Dean asked, looking at Sam carefully. 

_Yes_. Sam nodded, not trusting his voice anymore. 

Why was Dean doing this?

Why was Dean not pulling away? 

Why was Dean not throwing Sam out? 

Holy shit- Was Dean moving closer? Yes, he was and his hand was moving further up Sam’s leg. The heat blazed up his calf and wrapped around his knee, making him lock up his leg. 

Dean immediately pulled his hand up.

 _Stupid,_ Sam cursed at himself. “I’m sorry,” he blurted. Sam felt a spine-shaking tremble climb up his back, but it wasn’t an unpleasant one this time. Those have mostly abided. This felt… “It’s nice,” Sam whispered. 

“Yeah?” Dean’s playboy smirk was suddenly very clear and Sam felt two conflicting emotions: horror and arousal. Horror because of his arousal because what the fuck was Dean doing? He _never_ touched or looked at Sam like this. It was always directed at other people, at other _girls._ Just because Sam was wearing a dress, that didn’t mean he’s suddenly grown boobs and his dick fell off. 

“What’s happening?” Sam asked, his voice scratchy. 

Sam almost pulled his legs back, his insecurities pulling their plastic-bag self over his head to cut off Sam’s lungs to the oxygen they needed. His hands shook so he moved them to pull his skirt down, feeling the soft fabric of the inside brush his, thankfully, still flaccid cock. 

“Sammy…” Dean sighed, pulling his hand away. He didn’t back away but he didn’t meet Sam’s eyes. 

It didn’t help Sam’s inter battle. This was where his older brother says, _Look Sammy, I can’t have such a fucking_ queer _of a brother around._ Sam’s eyes burned, he was sure he’d start crying again, but no tears came because his eyes were too cried out. So Sam sat there for the minute or so it took Dean to gather the courage to say what he needed to. The young boy was trembling again. 

Sam could see Dean was trying to find the words. Dean’s mouth opened and then closed again. His eyebrows scrunch together and Sam wanted to look away, but he had to watch. It would probably be the last time he saw his brother’s beautiful face. 

“I..” he croaked. 

Why was this so hard for him? If he wanted Sam gone all he had to do was fucking say- 

“The way you look…” he trailed off and his eyes burned into Sam’s body. It made the teenager squirm. “I don’t… I _can’t.._ ”

Sam’s frustration at his brother’s lack of words built. He just needed Dean to _say_ it so he can gather his things and leave. The most he can ask of Dean is that he lets Sam take his things. God, if he were to be tossed out tonight he’d probably head into town and buy new clothes. He’d ignore all the looks from civilians and just fucking piece his life together. Or attempt to, at least. 

“You can’t what?” Sam pressed. _You can’t even look at me, Dean._ Sam’s thoughts spoke smoothly and filled his head with this poison. _You can’t fucking look at your disgrace of a brother, I know, Dean. I_ fucking _know. Please, just say it. Say it so I can leave. So I can-_

“I can’t handle it,” Dean’s voice was merely a whisper. Sam had to lean forward - the skirt of the dress pulling up to reveal more of his thighs, pretty soon it will be exposing his junk, too bad the teenager didn’t care - to even hear his brother. “I know I _shouldn’t_ but, Sam, I feel so…” Dean’s breath hitches and it stops Sam cold, “...out of control.”

What did that even mean? Sam’s eyebrows knitted together as he tried to figure it out. He didn’t give it too much thought before he gave up. Dean has always been a confusing person, and the fact that he was leaving himself so open still shocked Sam, but his brother was willing to talk, Sam was sure as hell going to listen. “Out of control?” Sam echoed. 

Dean finally met Sam’s eyes, and he looked so helpless. “Yes,” he hissed. 

“I don’t… I don’t understand…” 

Dean groaned and rubbed at his head. 

Sam held his breath. 

There was a tense moment. Dean’s hands were shaking. He was nervous, that sent a thrill through Sam. Why? He had no idea, but his bad feelings started to ease up. Dean didn’t look ready to throw Sam out, he seemed to be warring with himself. 

“Dean?” Sam encouraged. 

“Sammy,” he scooted forward even more - _only inches between them_ \- and sat on his knees. He toward over Sam and the sixteen-year-old had to crank his neck back look at him. Looking up at his brother reminded him of his fantasy earlier with Dean in the shower. Looking up at Dean while he grabbed a hold of Sam and yanked him where he needed him, so Sam’s mouth opened and _his thick cock slid past his lips and teeth, choking him as the tip rammed into the back of his throat._

Sam’s cock twitched when he looked up and met Dean’s eyes. They weren’t far apart anymore, Dean was leaning closer. 

“Sam,” Dean said his name again, sending more shivers down the younger’s spine. God, if Sam wasn’t careful he was going to pop a full boner right here. 

Did Dean get off on being above Sam like this? Did it make him feel more powerful?

Sam swallowed back the moan that was suddenly there. 

“Dean,” Sam was helpless to whisper back. What was happening? They needed to talk, not… not _this._

“I want to kiss you,” Dean groaned, moving closer. 

Sam’s world slowed the fuck down. His breath stopped like it was punched out of him or something, and his head was spinning. Holy shit, Dean was leaning closer and his eyes were closed. On reflex, Sam closed his, too. 

“Stop me,” Dean muttered. 

“What..” Sam phrased it like a question, but it was barely a fluttery whisper. The younger one was still leaning in, they were close, _real_ close now. Sam felt Dean’s breath ghosting over his mouth and nose. It’s fast and unsteady huffs of air that flutters Sam’s eyelids and he doesn’t want to pull away. 

“We-we can’t…” Dean stops, Sam’s eyes flicked open. 

Dean looks _scared_. The look doesn’t help Sam’s steady-breathing at all. His brother’s shoulders are curved inward, his eyes look at his hands - the ones that weren’t touching Sam anymore and were in his own lap - and his lower lip trembled. Sam saw a spot of spit on his full lip, he wanted to reach out and taste it. He wouldn’t do it though, not with Dean looking so ready to run. 

“But we can,” Sam says, his voice a strong whisper. It’s so unlike what he is thinking or feeling. Seriously, he’s experienced the most vicious emotional whiplash this evening. Too bad he couldn’t just pause and take a breather because if he stopped now and let Dean go… he’d never see this kind of vulnerability again. 

“Stop me,” Dean meets Sam’s eyes. 

His eyes and vividly green, and Sam’s been looking there his entire life. His _entire_ life and yet, he’s never seen them like this. The black pupils were bigger than normal, the bright emerald green was a thick ring all around. Sam has stared at his brother’s face through all of its varied expressions, has thought and dreamed about it even more. And never, with his brother’s body heat permeating the air for Sam’s cold skin to soak up, has Sam ever seen his brother like this. 

“No,” Sam’s voice did not shake. He wasn’t trembling anymore. 

Dean’s lips parted, making a small noise. Sam’s eyes tracked Dean’s tongue as it came out and left a gleam over his lips. They were ridiculous, Sam sometimes thought, his kissable Dean’s lips were. They were thick enough to promise a comfort and Sam knew his brother was skilled enough to promise a good time. Dean was showing just a glimpse of his white, straight teeth and Sam saw his tongue tucked up behind them. 

The younger was too busy watching Dean’s lips to see his hand come up. His right hand, not the one that had been sending goosebumps to rise up Sam’s legs, but his other. It came up and touched Sam’s neck with just the fingertips of the first three fingers. 

“Stop me, Sammy,” Dean said as his hand grew more confident. Dean let his knuckles brush against his brother’s pulsing throat. His touch was hot, burning as it lit up and path on Sam’s skin. 

“No,” Sam tilted his chin up slightly, letting Dean’s large hand cradle Sam’s jaw. These fingers extended into the younger’s hairline. Sam dropped his head into Dean’s palm. He was sure he’d be purring if he could. His touch felt nice, it was warm and comforting.

As it is, Sam closed his eyes and drifted for a moment. “Never,” he whispered sleepily.

Dean’s other hand touched Sam’s leg again, above the knee. The hairs on Sam’s leg raised up and a pleasant shiver ran up his spine, one that Dean undoubtedly felt. Sam didn’t open his eyes, but he blindly reached forward. His fingertips first grazed the collar of Dean’s t-shirt. At first, the teenager took a second for himself and rubbed his fingertips against his brother’s collarbone and felt the damp skin there, the hard bone. Then his fingertips gripped the collar of the shirt, his fingers trapping a bit of the fabric in his fist, and pulling Dean forward. 

“Sam,” Dean gasped, his mouth pressing openly to Sam’s. 

Sam didn’t let go, his other hand came up to grab onto Dean wherever he could get him, which was his shoulder. He wasn’t letting go. His inexperienced mouth moved, encouraging Dean to guide him. 

His older brother did not let him down. Dean’s mouth pressed close, lips together now, and his hand tilted Sam’s head the way he wanted. His fingers tangled in Sam’s short strands, the sensitivity in his scalp detecting every pull that sent zaps of arousal to Sam’s cock. Yeah, he was definitely hard now. 

“Dean,” Sam whined when he tried to pull the other way. He wanted Dean to open his mouth, to speed up the kiss, but his brother hadn’t wanted that so he tugged Sam back by his hair. Sam’s body shook when he did that, the pleasure prickling around his head, making him light-headed. 

“You like that?” Dean whispers against his brother’s lips. His hand moves further into the back of Sam’s head and he grabs more hair to yank on. Sam’s hips jerk forward as an instant reaction, a moan falling into Dean’s mouth. 

Both boys pulled back and Sam watched Dean look down, and yeah, Sam knew what his brother saw. In all his shifting, Sam’s dress had ridden up and his hard cock was standing loud and proud for Dean to see, the fabric bunched up around the boy’s hips. 

“Fuck,” Dean gasped when he saw it. 

There was another stab of arousal, making Sam’s cock twitch. God, he wanted Dean to touch him. He just didn’t know how to say that. 

“Dean…” Sam whined, sounding out the vowels. He tried to pull Dean forward again but the older boy resisted. Sam would have better luck trying to move a brick wall. Was Dean just playing with Sam? Was all of this a _joke_?

Dean whispered his brother’s name. “What…?” He refused to meet Sam’s eyes. 

Of all things to say, _of all things,_ Sam’s brain fogs up with the possibility that this all could be a prank. His heart beating faster than it has ever before and his lips move numbly, “Do you want me?”

The question is barely there, in fact, if they hadn’t been so close, Sam was sure his brother wouldn’t have heard it. Sam wouldn’t have been able to make his voice any louder and he wouldn’t be able to stop his heart beating and the sweat that was forming in his palms and the back of his neck. He clenched his hands, both still curled in Dean’s shirt, as panic set his claws in the longer Dean took to answer. 

“De _an_ ,” Sam’s voice cracked at the end of the name. He unclenched his hands and slowly brought them back. Even with Dean so close and the phantom feeling of his lips still pressed against Sam’s, the teenager’s erection was waning. Sam’s hands shook as he lifted his hips up and yanked his skirt back down, covering himself up. Sam watched Dean watch his every move. 

“Please,” Sam begged, “say something.” 

Two stuttering breaths later, Dean answered with a coarse whisper. “I don’t.. What do you want me to say, Sammy?” 

That stung Sam. Each word pressing sharply into the boy’s heart and not letting go. His eyes welled up with tears again, just when he thought he was all cried out. Tonight has been one hell of an emotional roller coaster. It was fine now, though, Sam told himself, _Dean doesn’t know what to say. So it’s just goddamn fine._

Sam nodded as his tears fell. Dean was still watching his brother. And he watched his brother get up and unfold his legs, Dean’s hand that had been on Sam’s leg before slid up when the boy stood up. The muscles cramped up before releasing as Sam stretched them again. His back ached and his head hurt. At this point, he just wanted to be alone and unconscious. “It’s fine, Dean,” he mumbled and stepped past his brother. 

Dean didn’t say anything. 

Sam remained silent as well. Something bitter was welling up inside of Sam, and the longer the dress was on the heavier he felt with it. If Dean didn’t want to say anything and he didn’t want to react at all, then fine, Sam would just go elsewhere. Sam couldn’t be here anymore, at least, not tonight. 

“Sam..” Dean’s voice called after the kid when he grabbed his duffle bag and walked out of the bathroom. 

Sam didn’t say anything, he just suppressed a sob by holding his breath. When the feeling passed he clenched his teeth and felt the immense dissatisfaction of not releasing it. Everything was fine, though. Sam would be fine. He just had to keep telling himself that he would be just fucking _fine._

“Sam!” Dean called and Sam heard his brother stand up. 

Sam walked over to his bed and sets his stuff down, he was standing in between the two beds with his back to the bathroom door. He thinks for a minute about going back into the bathroom because now Dean is walking out. He needs to take this thing off. He no longer likes the feeling of it on his body and no longer finds himself now feels attractive in it. There is no more excitement or arousal. There is only the quietude of how fine he was. 

‘“Are you hearin’ me?” Dean stood on the other side of the room, still by the bathroom. Sam barely threw a glance his way, he was suddenly so tired. He didn’t want to deal with this anymore. It was evident Dean wasn’t going to kick Sam to the curb or he would have done it by now, so Sam just wanted to sleep. So that tomorrow he could get rid of all the feminine clothes and supplies now that his fantasies have been crushed and obliterated. 

“You don’t have to say anything, Dean.” 

Sam pulled out clothes from his duffle, bending over a little to dig under all of the other clothes he’d been collecting recently. He was too occupied with distracting himself from Dean that he didn’t know when Dean crossed the room and was standing next to Sam. 

“It’s not fine, Sam. I shouldn’t have-” he stopped himself, unable to finish. 

A sour chuckle burned its way out of Sam’s breath, it didn’t last longer than a breath. Dean’s behavior wasn’t surprising and that was the kicker, wasn’t it? How emotionally detached his brother was and how Sam just wanted to know what he was thinking?

Sam refused to look at his brother, instead, he just reached behind him to unzip the back of the dress. If Dean wanted to stand this close and see all of Sam, then whatever, Sam was just _fine_ with it. Except, his fingers just touched the zipper, didn’t even fully enclose around the small metal tab, before he was being stopped. 

Dean’s hand grabbed at Sam’s. His brother’s breath was fluttering over Sam’s shoulder and bare neck. Goosebumps rose and spread quickly over his arms and legs, raising the hairs there. A shiver traveled up the teenager’s spine. 

“What are you doing?” Sam asked. Dean’s hand still held onto Sam’s, trapping his arm behind his back. It was a loose grip that Sam new about ten different ways to twist out of. He didn’t move though. 

“Don’t take it off,” Dean murmured. 

Then Sam felt his lips press into the skin behind his ear. Sam’s hold body jerked and he ripped his arm back. 

“You look-” 

Sam interrupted Dean by whipping around and shoving him back. Both of Sam’s hands pushed into Dean’s chest and the older one stumbled back. Dean’s arms reached out and pinwheeled by his sides for a second before his feet came out from underneath him. Dean landed on his own bed and bounced up and down a few times. He pushed himself to look up at his younger brother with a shocked look on his face, supporting himself on his elbows. 

“What the hell was-?” 

Sam didn’t even let him finish his question. “You, Dean-” Sam walked over and jabbed a finger into Dean’s chest, hard, “-need to figure your shit out.” 

“Whuh-ut?” Dean stuttered. His eyes zeroed in on the finger pressing into his chest hard enough to leave a bruise behind, he stared for a second and then looked back up at Sam. 

Sam was furious. Yes, he was still wearing a dress, but it did not cap his fury in the slightest. He did not feel guilty at all about what he looked like. He did not feel embarrassed. He didn’t feel any of this because how fucking dare Dean have so much power over Sam? How dare Sam get lost in the feeling of resentment and guilt that his brother had let him feel. 

“You fucking heard me.” Sam pulls his arm back and stands up straight, looking down at Dean. “This-” he gestures to the dress “-is something I have wanted for a while. This is something that I enjoy and living our lives, I’ve realized that those things come few and far in between.” 

Sam takes a deep breath and wipes his mouth. It was suddenly so filled with saliva and he didn’t want to think anymore about that. Still, Dean didn’t say anything. It only made Sam angrier. 

“You do not get to judge me on this because it’s what I want.” 

Sam finishes and stares at Dean. That’s it. That’s all he’s got to say and now he feels like a hollow shell. Everything that was on the inside was out, floating around the air. Dean would either accept him or he wouldn’t, but Sam was tired of not being himself because of Dean’s or Dad’s views. 

Dean sat up complete, looking and Sam. He took a deep breath and rubbed it down his face. “Sam,” he began. “I’m not going to judge you or-or tell you that you can’t.” His face was open and honest and Sam just stared, enraptured by his brother’s gaze. “I..I can’t ‘figure out my shit’ like you say. It-t’s not that easy. I don’t know how to, to _say_ it.” 

“But what are you trying to say?” Sam sits down on his bed. 

Dean looks at him, pleading with his eyes and Sam doesn’t know what to do with that. 

“Do you want me?” 

“Huh?” Dean’s question throws Sam off. 

“Do you want me?” Dean repeats, after a second, he raises his eyebrows. 

Sam stares at green irises and freckles. He stares at full lips and a long neck. He stares at short-cropped, tousled hair. He stares at wide shoulders and arms thick with muscles. He stares at his brother the drinks in his appearance. He’s as beautiful as ever. 

Sam thinks about all the time Dean’s aroused him. How fast Sam got off at the image of Dean. Of Dean’s face. Of Dean grabbing Sam’s hair. Of Dean doing things to Sam. Sam thinks about the jerkoff session he had earlier that day, of how he imagined choking on Dean’s cock and getting off on getting his hair pulled. 

Then he thought about _Dean._ He thought about himself coming home from a bad day at school and needing only to see Dean for his day to brighten. How Dean could always tell when Sam wasn’t okay and all he had to do is run a hand through his hair and say, “It’s all right, kiddo,” for Sam to believe it. He thought back to when he was younger and thunderstorms used to scare him at night. How he would shake and whimper in his own bed, too scared to move, before Dean would slip into his bed and wrap himself around his younger brother. How Sam would have no trouble sleeping after that. How he was so and irreversibly in love with Dean. 

Sam thought about all of this and he found his answer. “Yes, I do.” 

Dean’s lips quivered for a second before he was asking, “How?” 

“How?” Sam echoed and Dean nodded. 

_How_ don’t _I want you, Dean?_ Sam asked himself. There was probably no limit on how much Sam wanted Dean. There were no boundaries and no borders. Dean was everything to Sam, his only constant in his life. There was no way he could ever not love Dean. 

“I want…” Sam looked down at his hands in his lap. Why was he suddenly nervous? Where was the confidence he had moments ago? Sam wished it would come back and he wished Dean didn’t have such control over his emotions. 

“Yes?” Dean gently encouraged. Sam met his eyes and found strength in green emeralds. 

“I want everything.” Sam bit his lip and held his breath. 

Dean sighed and stood up. Sam’s heart stuttered and clenched tightly when he thought he was going to leave. Instead, the older boy just turned around and sat next to Sam. They weren’t touching, but Sam’s bare leg heated up with Dean’s body warmth. 

“I want everything, too,” Dean murmured. 

Sam’s lower lip trembled and he held back tears. Here was Dean, telling him everything he wanted. On one hand, he didn’t believe Dean. He didn’t believe that Dean could be messed up like he was. And then on another hand, it’s easy to remember the feel of Dean’s lips pressed against his own. Sam remembers the smell of Dean’s breath up close and how his moist breath had brushed over Sam’s face. How addicting it felt. How easy it was to kiss his brother as if it wasn’t one of Sam’s first kisses.

“Dean,” he said because it was the easiest. 

“I know it’s wrong,” Dean started, his shoulders slumped forward and looked away from Sam. The teenager could only see the side of Dean’s face and he could tell by the way he shifted away from Sam that he felt guilty. “And maybe we shouldn’t-” 

“Dean,” he stopped his older brother. Sam wondered if Dean’s guilt was an old emotion. How long has his brother thought about Sam this way? “I’m so done with morals, I don’t care what the world thinks. I care what _you_ think. We kissed earlier, but if you don’t want more…” Sam swallowed with a dry throat. “Then we don’t have to,” he finished.

“I don’t know…” 

Sam sighed impatiently. Dean stands up quickly and ran a hand through his short hair. He was a little irritated with Sam, which Sam saw by the way his brother glared at him. 

“Well, I’m sorry, Sam. I come back and find my kid brother in a fucking dress-” 

“ _That’s_ your issue with this,” Sam tried to interject. 

Dean continued on as if Sam had never spoken. “-and I’m trying to hide a fucking boner because he looks so good in it. And now you are telling me I’ve got to have every-fucking-thing figured out when two days ago I was still jerking it to the very _thought_ of having you!” Dean’s breathing hard, his chest rapidly expanding and falling. His eyes dance all over Sam where he still sits on the bed, rendered motionless by Dean’s outburst. 

“You what?” Sam’s voice was small with disbelief. 

Dean walked a few steps forward and a few back, pacing in front of Sam. “Yeah...” he mumbled, not stopping to look at him. Dean was shaking his head and grabbing at the front of his shirt and pulling it forward. Sam knew that was something he did when he was overwhelmed and part of him wanted to comfort his brother but he, too, was overcome with emotions. 

Sam stands up, trying to get eye level with Dean, “You think I look good?” 

Dean stops, startling Sam with the intensity behind his eyes. The older boy comes up and places his hands on Sam’s bare shoulders, His first two fingers tuck themselves under the straps of the dress and rub back and forth. Sam watches Dean watch Sam. The touch feels nice and he doesn’t want it to stop. 

“Sam, you look…” Sam waits with bated breath the few seconds it takes for Dean to continue, to find the right word. “ _Beautiful._ ”

Sam looks down at their feet - his bare and Dean’s covered by socks - he lets his hair cover his eyes as they become a little moist with happy tears. Sam takes a deep breath, feeling the dress move with his chest as he inhales, and starts to enjoy the feeling of the dress on him again. He likes the flowing skirt, the liberating wind he feels when he walks. He hasn’t had much time to walk around and just _feel_ the dress on him, but now that he takes a second, he feels beautiful. 

“Honest?” Sam asks. 

Dean’s closer than he was before. When Sam looks up, their noses brush. “Wouldn’t lie.” 

Then they are kissing again. Except, it’s not like last time. It’s not rushed lips and heated breaths. It’s still enough to send strikes of arousal through the teenager, after everything that’s happened, Sam still surprised that he’s able to get hard again. It must be Dean and how he is kissing. It’s slow, it’s sensual, its _love_. It’s Dean’s left hand moving to cup the back of Sam’s head and his other moves to his waist, tugging him closer. It’s Sam still being short enough that he has to crane his neck back to not lose contact. It’s Dean breaking away first to rub the tip of his nose along Sam’s jawline. 

“What are we…?” Sam trails off. It’s not a demand, it’s an honest question because he wants to know what the fuck they are doing? He wants to talk with Dean about this. Are they in a relationship? Are they exclusive? Are they even going to continue this? What even is this?

“Shh..” Dean murmurs and gently backs Sam up. 

The back of the teenager’s knees hit the bed and for a second, Sam is confused why Dean is still pushing because there is nowhere else for his to go. Then in the next second, when gravity starts pulling Sam down, the younger boy understands. He bounces on the bed a couple of times before Dean’s on him again, making them bouncing some more. 

“Dean,” Sam sighs. He didn’t have anything else to say besides his favorite word. 

Dean reaches down, his lips nuzzling Sam’s neck, and grips the back of Sam’s bare thighs. He pulls Sam up so that he is all of the way on the bed. Of course, Dean follows and peppers kisses across his face. Sam scrunches his face and Dean kisses him there on his nose. Sam didn’t know that Dean could be like this, he likes it. 

“You’ve had sex before, right, Sammy?” Dean asks, lining their hips up.

Sam’s hard again and so is Dean. The teenager moans and arches his neck so that the back of his head digs into the pillow. He loves the way Dean feels pressed against him, he knew he’d love it, but how quickly he’s becoming addicted surprises him. He crunches his eyes closed and moves his hips up to Dean’s, a soft sigh leaving his lips. It felt really good to do this with another person, especially Dean. 

Dean stops moving, waiting for his question to be answered. “Sammy?” he asks. 

“What?” his eyes flutter open and he looks at his brother. Dean’s cheeks are red and his eyes are open and looking at Sam. The younger grins and with one hand on his shoulder, he brings the other to Dean’s hair and tries to pull the older boy back in for more kisses. Sam heard the question, he just knows his answer won’t be one Dean will like. 

“Sam,” Dean allows himself to be pulled down. He kisses Sam again and the younger rubs his erection up against Dean’s jean-clad one. “C’mon, Sam. Answer me,” Dean begs. “Is this your first time?” 

“Dean, it doesn’t matter,” Sam wants Dean to just kiss him. Would he just kiss his little brother and make him forget about everything else? He wanted to drown in Dean and never swim back to the surface. 

“It does, though,” Dean sits up. At first, Sam doesn’t let go of Dean’s shoulder or head and starts to sit up with him, but then Dean grabs Sam’s hands in his own and lowers them. He doesn’t let go of Sam’s hands though, so the younger boy takes comfort in that. 

Sam sighs, this time with annoyance, “Fine. No, I have never had sex before, but that doesn’t change anything, okay?” Sam saw how unconvinced Dean was. Sam looked at him for a while, they both watched each other breathe for a few moments. 

Sam wanted to have sex with Dean, right now. And he knows by the large erection he felt - that hasn’t flagged at all, Sam might add - he knows Dean wants to too. Sam trusts Dean, he knows that Dean would never hurt Sam and knows that with his first time being with Dean, it will be amazing. 

“It does, though, Sam.” 

“No.” Sam looks at his brother seriously. “Dean, I trust you. I don’t want to trust anyone else with something like this. Please?” 

He must have gotten through to him because Dean’s lips quirk into a smile and he nods his head. Then he’s leaning closer to Sam and cocking his head to the side so that he can fit his lips against Sam’s. “Okay, Sam,” he murmurs and slides his lips against the other boy’s. 

Dean pushes his tongue up against Sam’s lower lip and it’s a foreign feeling, but not an unpleasant one, Sam parts his lips. Dean’s tongue traces Sam’s teeth and glides against his own. When a hand comes up and tangles in Sam’s hair, pulling it gently down so that Sam’s head jerks up, the teenager moans loudly into Dean’s mouth. 

“Fuck,” Dean curses, the word sounding so, so hot to Sam. 

Dean sits up, only breadths away from Sam’s mouth, and yanked on his hair again. Pleasure screams through the teenager and travels all through his body. His nipples tightened under the toilet paper still shoved inside his dress and arched his back as far as he could. Dean laughed, fucking _laughed,_ at Sam’s reaction. Sam panted out big breaths, his chest expanding and falling quickly. He grabs Dean’s head in both of his hands, burying his fingers in his hair, and slammed his brother’s lips back to his own. Sam moaned when Dean immediately licked into his mouth. 

“Sam,” Dean moaned. The older boy wrapped an arm under Sam and rolled them both over. Sam was given a second to readjust to this position before Dean was kissing him again, just as hungrily. 

Dean’s hand went back to his hair and yanked, harder this time, enjoying Sam’s reactions. Sam groaned and spread his legs, sliding his next to Dean’s hips. Sam sat up, putting a hand to Dean’s shoulder to shove him down when he tried to follow. 

Dean watched with curious eyes. 

Sam wanted to try something, he felt good and wanted his brother to feel good, too. Also, Sam felt slutty wearing _only_ the dress and wanted to use that high. He pressed his hips into Dean’s, their erections smashing together, and ground down with all of his weight. 

Dean shouted, jerking forward. Suddenly Dean was sitting up and Sam was still moving on his lap. “Fuck me,” the older one groaned. 

Sam’s hips jackknifed forward in response to Dean’s curse. Fuck, he remembered earlier, he remembered rubbing his dick against the couch and getting off on it. Dean’s jeans are rough like the couch had been. Sam grinned and brought his hand down between them to flip his skirt up. His dick was hard, red, and leaking. 

Dean groaned when he saw it, Sam smirked. Taking a hold of his dick was easy, feeling the familiar weight of it in his palm. He rubbed against the head to gather the pre-come there. Sam moaned and gripped himself closer to the base. Then he tilted his hips forward, pressed his dick into Dean’s through his jeans and fucking jerked forward. The sensitive head ran across the denim and both boys inhaled sharply. Sam laughed with how easy it was to rock back and forth. He loved the feeling, the coarseness of Dean’s jeans against his dick and the heat against his balls too. 

“Fuck, Sam,” Dean moaned, burying his nose into Sam’s hair. 

Sam felt his hands come up and grip his hips, not stopping him but just feeling the muscles move there. Sam opened his mouth and press it to Dean’s neck and rocked down hard again, his hips jerked and bucked and the pleasure was intense. “Oh, oh..” Sam panted out. 

“Feel good, huh?” Dean teased, licking up the sweat on Sam’s temple. That made Sam jerk harder on his lap. 

Sam released his cock and put his hand on Dean’s other shoulder, balancing himself. He slowed down to a slow grind, barely a conscious movement. “Show me, Dean,” Sam moaned. 

“Fuck yeah, baby.” Dean pulled back and started working on undoing the front of his jeans. Sam watched him, biting his lip in anticipation. “Anything for you, babe,” Dean continued, pulling down his zipper. “Anything for you when you ride me like that.” 

“You want me to ride you?” Sam asked, pressing his cheek into Dean’s temple while he watched Dean’s cock spring out of his shorts and curve up against his stomach. 

Sam might have never had sex before, but he certainly fucking imagined it. The image in this mind now struck him hard with arousal; himself on top like he was now, but instead of moving his cock into Dean’s he’d move so that Dean’s cock went _in and out of his ass_. Fuck, Sam wanted that. 

“Shit, Sam,” Dean pushed his hips forward. “Don’t say shit like that.” 

“Why not,” it was Sam’s turn to tease. Sam watched a fat drop of pre-come well up on the tip of the beautiful cock in front of him. Fuck, it looks so good and Sam wanted to fucking _lick_ it. 

Sam is flexible because of the sparring and exercises he does to keep in shape. He also does stretching on the side, making sure he can bend and twist smoothly. He can also bend his back far enough to get his mouth down by Dean’s dick. His tongue slurps up the pre-come at the head. 

Dean’s body spasms and his hips jerk up. Which would be fine, if his hands hadn’t immediately come down to Sam’s hair and push his little brother’s head down. 

Dean’s cock crammed itself into Sam’s mouth, the head forcing itself inside and stretching his lips and jaws apart. Sam kind of goes insane with pleasure. He breathes in through his nose and tries to go down farther, tonguing at the vein on the underside of his brother’s cock. His legs slide backward and he grinds his erection into the mattress. Hell yeah, he could get off on this. 

“Fuck, I’m sorry-” Dean starts, grabbing at his head to lift him up, his fingers tangling in Sam’s hair. 

Except, Sam’s head doesn’t budge. Instead, the teen succeeds in shoving himself farther down and the head of Dean’s cock touches the back of Sam’s throat. 

“Sammy!” Dean moans loud enough for Sam to feel it in his core. Sam can feel Dean’s thighs underneath him tense up like he’s holding back from moving his hips and putting his dick farther into Sam’s mouth and that’s just _wrong._

Sam pulls up, leaving his mouth open to suck in large breaths. He meets Dean’s eyes and slowly slides off of Dean’s lap. The teenager stands up on the floor on legs that only wobble a little, his dress falling over his crotch again, covering his junk. 

“Sammy?” Dean asks. 

Still not saying anything, not trusting his already rough throat, but wanting so fucking _bad._ He starts sinking to the floor, slowly dropping to his knees. Dean watches him go until his chin touches his chest, eyes still on his little brother. 

Fuck, Sam feels really bad on the floor like this. _Like a bad girl,_ his mind offers and Sam’s dick twitches, hard enough that he’s afraid he was going to blow his load right there. 

“Yeah,” Dean slides over to that edge of the bed, throwing his legs over each side of the mattress. Sam’s sitting on his knees in between Dean’s legs, smelling the scent of his arousal. Oh God, how did he get here? He never wanted to leave. 

Sam nodded at Dean, only tilting his head up slightly, looking at Dean with hooded eyes. Shit, he almost grinned, realizing just the effects he had on his older brother. 

“You wanna suck my dick, Sam?” Dean’s panting hard, but his voice was even still. Sam wanted that to change. 

He shook his head no. Then let a small smile play on his lips. Sam watched his older brother's confused expression for a second before he cleared his throat and in a harsh voice say, “I want you to fuck my throat.”

Dean inhales a deep breath sharp enough for it to be considered a gasp, eyes widening. Sam noticed the tiny jerk his hips made and how his dick swung back and forth, Sam licked his lips. That caused Dean to openly cursed. Then he was standing up and towering over Sam, Sam’s legs spread open. 

“You want this?” Dean looked down at his brother with heavily lidded eyes. 

“Please,” Sam moaned. He wanted Dean to understand that Sam wanted to be _used._ “Don’t hold anything back,” Sam blinked up at his brother. 

“You have no idea how you look right now, Sammy. So perfect for me.” 

Then Dean was lining his cock up with Sam’s mouth, the head rubbing against Sam’s bottom lip. And Sam was tired of waiting, he wanted that dick in his mouth _now._ So the teenage boy rose on his heels and swallowed Dean’s dick halfway.

“Oh, Sammy!” Dean shouted and when Sam looked up again, he saw his brother’s head thrown back and his mouth slack with pleasure. 

Sam hummed around his mouthful of dick and swallowed the spit and pre-come gathered in the back of his mouth. He felt his mouth squeeze around the hard flesh there and pleasure zinged down his spine when he heard Dean whine, fucking _whine_ , with pleasure. 

Fuck, Sam wanted to hear that again. The younger reached up and grabbed Dean’s hands that were clenched by his sides. Sam focussed on breathing with Dean’s thick, heavy cock in his mouth and brought Dean’s hands to his own hair. He really wanted Dean to fuck him up. Dean immediately grabbed handfuls of Sam’s hair and squeezed, pulling delicious pleasure from his scalp. Sam’s hips jerked forward as his dick fucking jerked and he thought he’d come right then, Sam screamed to the dick effectively cutting off his air in the most delicious of ways. 

Dean pushed in and out of Sam’s throat. He was still being gently though, Sam could tell in how tense his legs were. Shit, Sam wanted his brother to just give in and shove his dick down Sam’s throat. 

Dean pumped in, Sam’s left arm reached around and grabbed at the back of Dean’s jeans and pulled him forward. Sam’s top lip rubbed against Dean’s pubes and Sam spread his legs farther apart. He churned his hips in circles, the fabric of the dress dragging against his cock the only friction he got. 

With his other hand, Sam reached up and pinched his nipples through the dress. This made him gasp and everything in him clenched. He felt his ass clench when Dean’s dick twitched in his mouth. One of these days, Sam would have this beautiful cock in his ass. 

Distantly, Dean gasped out a warning that he was about to come. Sam, curious to know what his cum would taste like, he pulled off Dean’s dick almost all of the way and flicked his tongue against the tip, digging it into the slit. 

“Fuck, fuck, shit.” Dean’s hips jerked forward and Sam moaned when Dean’s dick was forced down his throat. _Yes,_ a voice crowed from the back of Sam’s fucked up head, _this is what we wanted!_ “Sam!” Dean cried out and Sam felt the dick in his mouth lurch again. 

Sam’s hips twitched forward and his dick di explode then. _Shit, shit, shit,_ Sam again screamed around the dick that was crammed into his mouth. White went off like fireworks behind his eyelids and his whole body locked up. His cock twitched and emptied itself on the carpet and Sam swung his hips in the air, fucking into nothing. 

After his orgasm passed, he pulled off to the tip and suckled there for a few breaths. His eyes were leaking tears and he couldn’t tell if it was from choking on Dean’s dick or his epic orgasm. He decided he didn’t care and swallowed Dean back down, so addicted to the feeling. 

Sam took his hand from his chest to the base of his brother’s cock and pumped his fist. When he squeezed him, Dean jackknifed forward and crowded into Sam’s mouth again. Dean moaned openly and wantonly, announcing to the whole fucking motel that he was coming. 

Sam couldn’t breathe, unable to pull air into his throat past the dick there, he sputtered and tears and spit ran down his face. Dean yanked himself back and Sam swallowed what was in his mouth, his tongue enjoying the salty, bitter taste of Dean’s cum. He opened his mouth to breath and accept anything else Dean has to offer. His dick spurted a couple more times, the streams arching into the air and mostly landing in the boy's mouth, some of it his chin, nose, and cheeks. 

“Fuck,” Dean panted like he just ran a few miles without a break. 

Sam grinned up at him. 

Dean dropped to his knees in front of Sam and flipped the skirt of the dress up, probably expecting Sam’s hard dick there so that he could get his little brother off. Instead, he gasps in surprise when they both look down to see Sam’s soft cock resting against his right thigh and a mess of cooling cum on the motel’s carpet. 

“Shit, Sam,” Dean blurted out.

Sam looked up to meet his eyes and instead was attacked by Dean’s lips on his own. The kiss was rushed and sparked another hint of arousal down Sam’s spine, but it was merely a leftover of the freaking epic orgasm he just had. 

Dean’s cheeks smeared his own cum in between their faces and his tongue chased after the taste in Sam’s mouth. It was a while before either of them pulled away, but Sam still hasn’t fully caught his breath and needed to breathe then. They pulled away, slightly sticking together from the cooling cum on their cheeks and it made them both laugh. 

“Here,” Dean said, he reached up to the back of his neck and pulled off his t-shirt. He surprised Sam by licking it to wet it down and then proceeding to wipe Sam’s face clean with it. 

“Thank you,” Sam said seriously when Dean finished. His throat hurt some, and his head hurt because his jaw had been forced open so wide, but it was a pleasant sort of pain. He enjoyed the ache he felt. 

“You okay?” Dean asked some time later. 

He was standing from where he took care of the spoiled shirt. He has since done up his pants and the blush that had stained his cheeks when he came has subsided. Dean extended his hand down to help Sam up off the ground. 

Sam nodded and grabbed a hold of Dean’s hand. He was fine and now was just tired. “I do want out of this, though,” he said and reached behind him for the zipper. 

“Here,” Dean mumbled, stepping up behind him. 

Sam felt his brother’s hands undo the zipper and the dress loosens and starts to fall off his shoulders and Sam’s arms come up to catch it, but Dean’s fingers start to drag it off of his body. Dean follows the dress with his hands as it slips over Sam’s shoulders and down his sides. 

“So beautiful,” Dean murmurs, his lips pressing into Sam’s bare shoulder. 

The dress was around his ankles on the floor. Dean touched his sides and his hips, his touch light and soothing. Dean hummed and explored more of Sam’s body. He let him, too, it felt nice. Goosebumps rose up on his skin and Dean’s breath tickled his ear and the side of his neck. 

“Am not,” Sam argued Dean’s earlier assessment. 

“Am too,” Dean spoke in a hushed tone, playfully arguing with Sam. 

Sam turned around in Dean’s arms and looked at his brother with a straight face. Sam felt his hands on his bare hips, fingers squeezing and pulling him closer. Sam pouted harder, sticking his bottom lip out. 

“What?” Dean asked. Sam thought he looks good with that sated, goofy look on his face. It suited him and made Sam fall just a little bit more in love with his brother. 

Sam broke and smiled at his brother. “You’re beautiful _-er._ ” 

Dean’s smile light up the room. Sam has never been into that sappy, romance shit, but he’s also never felt like this. He’s never felt this overwhelming calm and happy being in Dean’s arms. 

“Nu-uh,” Dean laughed, leaning in to kiss Sam’s neck. His hands tickled Sam’s side and made the teenager wiggle out of his grasp. 

Sam didn’t realize how close to the side of the bed they were and when he got out of Dean’s grip, he tripped over his dress and landed on the bed. They both were laughing and Sam’s cheeks hurt from smiling so much. All in all, Sam was glad he tried that damn dress on. 

**Author's Note:**

> Tell me what you think! This was my first Wincest fic, how did I do? Please, leave comments, kudos, or both. I greatly appreciate it!!
> 
> A new thing that I would like to mention is that I have a Tumblr now! It is https://only-useless-fanfictions.tumblr.com/ and I would very much appreciate the follow! I'm still really new and have no idea what I am doing, lol, but I'm on the map!
> 
> Something else that I'm not sure many people know about me is that I take prompts! I can write just about anything for Supernatural, any pairing or kinks. You can comment your prompt down below or email me at uselessfanfictions.writing@gmail.com or you can hit me up through Tumblr! Any way that I get the prompt is great, and I will let you know if I can do it.
> 
> Thank you all for reading, you are all very wonderful!


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